Hydrochloric Acid → Methyl 4-((methylamino)methyl)benzoate hydrochloride

Participants

Reaction Steps

To 12.2 g of the compound obtained in step (1-2) above was added 20 ml of an ethyl acetate solution of 4N hydrochloric acid under ice-cooling and after stirring the mixture for one hour, the crystals formed were collected by filtration to provide 6.8 g (yield 90%) of 4-(N-methylaminomethyl)benzoic acid methyl ester hydrochloride. Then, 6.5 g of the crystals thus obtained was dissolved in 30 ml of DMF and 4.2 ml of triethylamine and 5.0 g of (S)-2-methylbutyl bromide were added to the solution under ice-cooling. Then, 1.3 g of 60% sodium hydride was added little by little to the solution and the mixture was heated to 80° C. for from 1 to 2 hours. After cooling, the reaction mixture was diluted with 80 ml of diethyl ether and 5 ml of purified water was added dropwise slowly to the solution. The organic layer formed was collected and, after successively being washed with 20 ml of purified water, 20 ml of a saturated aqueous sodium hydrogen carbonate solution, and then 20 ml of a saturated aqueous sodium chloride solution, dried with magnesium sulfate, and then the solvent was distilled off under reduced pressure.

Provenance & Evidence